C-Nucleophiles
Name | Solvent |
Reactivity Parameters |
Classification |
Reference (title or year) |
---|---|---|---|---|
1-((diphenylmethylene)amino)-2-ethoxy-2-oxoethan-1-ide (in DMSO) | DMSO | N Param.: 26.95 sN Param.: 0.52 | Tetrahedron 2019, 75, 459-463 10.1016/j.tet.2018.1[...] | |
2-(tert-butoxy)-1-((diphenylmethylene)amino)-2-oxoethan-1-ide (in DMSO) | DMSO | N Param.: 27.77 sN Param.: 0.47 | Tetrahedron 2019, 75, 459-463 10.1016/j.tet.2018.1[...] | |
1-(benzylideneamino)-2-ethoxy-2-oxoethan-1-ide (in DMSO) | DMSO | N Param.: 29.10 sN Param.: 0.50 | Tetrahedron 2019, 75, 459-463 10.1016/j.tet.2018.1[...] | |
1-((4-chlorobenzylidene)amino)-2-ethoxy-2-oxoethan-1-ide (in DMSO) | DMSO | N Param.: 29.02 sN Param.: 0.49 | Tetrahedron 2019, 75, 459-463 10.1016/j.tet.2018.1[...] | |
2-(benzylideneamino)-1-ethoxy-1-oxopropan-2-ide (in DMSO) | DMSO | N Param.: 30.82 sN Param.: 0.41 | Tetrahedron 2019, 75, 459-463 10.1016/j.tet.2018.1[...] | |
cyano((diphenylmethylene)amino)methanide | DMSO | N Param.: 29.50 sN Param.: 0.50 | Tetrahedron 2019, 75, 459-463 10.1016/j.tet.2018.1[...] | |
(Z)-1,2-diphenyl-1-(trimethylsiloxy)ethene (in MeCN) | MeCN | N Param.: 3.00 sN Param.: 0.83 | Synthesis 2019, 51, 1157-1170 10.1055/s-0037-1611634 | |
(Z)-1-phenyl-1-(trimethylsiloxy)propene (in MeCN) | MeCN | N Param.: 5.18 sN Param.: 0.94 | Synthesis 2019, 51, 1157-1170 10.1055/s-0037-1611634 | |
3-(trimethylsiloxy)-1H-indene (in MeCN) | MeCN | N Param.: 7.32 sN Param.: 0.82 | Synthesis 2019, 51, 1157-1170 10.1055/s-0037-1611634 | |
1-(trimethylsiloxy)-3,4-dihydronaphthalene (in MeCN) | MeCN | N Param.: 5.06 sN Param.: 0.91 | Synthesis 2019, 51, 1157-1170 10.1055/s-0037-1611634 | |
3-pyrrolidino-1H-indene (in MeCN) | MeCN | N Param.: 15.27 sN Param.: 0.93 | Synthesis 2019, 51, 1157-1170 10.1055/s-0037-1611634 | |
1-pyrrolidino-3,4-dihydronaphthalene (in MeCN) | MeCN | N Param.: 14.09 sN Param.: 0.66 | Synthesis 2019, 51, 1157-1170 10.1055/s-0037-1611634 | |
diazocyclopentadiene (in CH2Cl2) | dichloromethane | N Param.: 4.84 sN Param.: 1.06 | Synthesis 2023, 55, 354-358 10.1055/s-0041-1737327 | |
allyltris(trimethylsilyl)silane | dichloromethane | N Param.: 1.95 sN Param.: 0.98 | Org. Lett. 2010, 12, 5206-5209 10.1021/ol102220e | |
(2-methylallyl)tris(trimethylsilyl)silane | dichloromethane | N Param.: 4.63 sN Param.: 0.87 | Org. Lett. 2010, 12, 5206-5209 10.1021/ol102220e | |
2-(tris(trimethylsilyl)siloxy)propene | dichloromethane | N Param.: 6.04 sN Param.: 0.82 | Org. Lett. 2010, 12, 5206-5209 10.1021/ol102220e | |
1-(tris(trimethylsilyl)siloxy)cyclohexene | dichloromethane | N Param.: 5.07 sN Param.: 0.91 | Org. Lett. 2010, 12, 5206-5209 10.1021/ol102220e | |
(tris(trimethylsilyl)siloxy)ethene | dichloromethane | N Param.: 4.01 sN Param.: 0.83 | Org. Lett. 2010, 12, 5206-5209 10.1021/ol102220e | |
1-(perfluorophenyl)-1-(trimethylsiloxy)ethene | dichloromethane | N Param.: 1.47 sN Param.: 0.89 | Org. Lett. 2012, 14, 3990-3993 10.1021/ol301766w | |
3,3,3-trifluoro-2-(trimethylsiloxy)propene | dichloromethane | N Param.: -2.94 sN Param.: 1.11 | Org. Lett. 2012, 14, 3990-3993 10.1021/ol301766w | |
(3,3,4,4,5,5,6,6,7,7,7-undecafluoro)-2-(trimethylsiloxy)hept-1-ene | dichloromethane | N Param.: -3.52 sN Param.: 1.17 | Org. Lett. 2012, 14, 3990-3993 10.1021/ol301766w | |
lithium 2-benzyl-4,4,5,5-tetramethyl-2-phenyl-1,3,2-dioxaborolan-2-uide (in MeCN) | MeCN | N Param.: 8.92 sN Param.: 0.70 | Org. Lett. 2015, 17, 2614-2617 10.1021/acs.orglett.[...] | |
lithium 4,4,5,5-tetramethyl-2-phenyl-2-(1-phenylethyl)-1,3,2-dioxaborolan-2-uide (in MeCN) | MeCN | N Param.: 10.97 sN Param.: 0.63 | Org. Lett. 2015, 17, 2614-2617 10.1021/acs.orglett.[...] | |
lithium 2-benzyl-4,4,5,5-tetramethyl-2-(4-(trifluoromethyl)phenyl)-1,3,2-dioxaborolan-2-uide (in MeCN) | MeCN | N Param.: 7.15 sN Param.: 0.77 | Org. Lett. 2015, 17, 2614-2617 10.1021/acs.orglett.[...] | |
lithium 4,4,5,5-tetramethyl-2-(1-phenylethyl)-2-(4-(trifluoromethyl)phenyl)-1,3,2-dioxaborolan-2-uide (in MeCN) | MeCN | N Param.: 8.56 sN Param.: 0.76 | Org. Lett. 2015, 17, 2614-2617 10.1021/acs.orglett.[...] | |
lithium 2-(3,5-bis(trifluoromethyl)phenyl)-4,4,5,5-tetramethyl-2-(1-phenylethyl)-1,3,2-dioxaborolan-2-uide (in MeCN) | MeCN | N Param.: 7.46 sN Param.: 0.76 | Org. Lett. 2015, 17, 2614-2617 10.1021/acs.orglett.[...] | |
lithium 2-benzyl-2-(3,5-bis(trifluoromethyl)phenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-uide (in MeCN) | MeCN | N Param.: 6.30 sN Param.: 0.78 | Org. Lett. 2015, 17, 2614-2617 10.1021/acs.orglett.[...] | |
lithium 2-isopropyl-4,4,5,5-tetramethyl-2-(4-(trifluoromethyl)phenyl)-1,3,2-dioxaborolan-2-uide (in MeCN) | MeCN | N Param.: 6.63 sN Param.: 0.75 | Org. Lett. 2015, 17, 2614-2617 10.1021/acs.orglett.[...] | |
lithium 2-cyclopropyl-4,4,5,5-tetramethyl-2-(4-(trifluoromethyl)phenyl)-1,3,2-dioxaborolan-2-uide (in MeCN) | MeCN | N Param.: 7.72 sN Param.: 0.75 | Org. Lett. 2015, 17, 2614-2617 10.1021/acs.orglett.[...] | |
lithium 2-ethyl-4,4,5,5-tetramethyl-2-(4-(trifluoromethyl)phenyl)-1,3,2-dioxaborolan-2-uide (in MeCN) | MeCN | N Param.: 7.68 sN Param.: 0.78 | Org. Lett. 2015, 17, 2614-2617 10.1021/acs.orglett.[...] | |
lithium 5,5-dimethyl-2-(1-phenylethyl)-2-(4-(trifluoromethyl)phenyl)-1,3,2-dioxaborinan-2-uide (in MeCN) | MeCN | N Param.: 11.29 sN Param.: 0.76 | Org. Lett. 2015, 17, 2614-2617 10.1021/acs.orglett.[...] | |
3-mesityl-1-methyl-1H-imidazol-3-ium-2-ide (in THF) | THF | N Param.: 21.50 sN Param.: 0.45 | Org. Lett. 2016, 18, 3566-3569 10.1021/acs.orglett.[...] | |
3-(tert-butyl)-1-methyl-1H-imidazol-3-ium-2-ide (in THF) | THF | N Param.: 16.54 sN Param.: 0.47 | Org. Lett. 2016, 18, 3566-3569 10.1021/acs.orglett.[...] | |
3-(4-methoxyphenyl)-1-methyl-1H-imidazol-3-ium-2-ide (in THF) | THF | N Param.: 20.41 sN Param.: 0.46 | Org. Lett. 2016, 18, 3566-3569 10.1021/acs.orglett.[...] | |
3-(2,6-dimethoxyphenyl)-1-methyl-1H-imidazol-3-ium-2-ide (in THF) | THF | N Param.: 23.00 sN Param.: 0.46 | Org. Lett. 2016, 18, 3566-3569 10.1021/acs.orglett.[...] | |
anion of (4-NO2-C6H4)CH2SO2Ph (in DMSO) | DMSO | N Param.: 18.50 sN Param.: 0.75 | Org. Biomol. Chem. 2008, 6, 3052-3058 10.1039/b805604h | |
anion of (4-CN-C6H4)CH2SO2Ph (in DMSO) | DMSO | N Param.: 22.60 sN Param.: 0.57 | Org. Biomol. Chem. 2008, 6, 3052-3058 10.1039/b805604h | |
anion of (4-CF3-C6H4)CH2SO2Ph (in DMSO) | DMSO | N Param.: 24.30 sN Param.: 0.51 | Org. Biomol. Chem. 2008, 6, 3052-3058 10.1039/b805604h | |
N-vinylcarbazole | dichloromethane | N Param.: 5.02 sN Param.: 0.94 | Macromolecules 2002, 35, 5454-5458 10.1021/ma020306l | |
2,4,6-trimethylstyrene | dichloromethane | N Param.: 0.68 sN Param.: 1.09 | Macromolecules 2005, 38, 33-40 10.1021/ma048389o | |
Indole | dichloromethane | N Param.: 5.55 sN Param.: 1.09 | J. Org. Chem. 2006, 71, 9088-9095 10.1021/jo0614339 | |
N-methylindole | dichloromethane | N Param.: 5.75 sN Param.: 1.23 | J. Org. Chem. 2006, 71, 9088-9095 10.1021/jo0614339 | |
1,2-dimethylindole | dichloromethane | N Param.: 6.54 sN Param.: 1.10 | J. Org. Chem. 2006, 71, 9088-9095 10.1021/jo0614339 | |
2-(bis(trimethylsiloxy)amino)propene | dichloromethane | N Param.: 4.76 sN Param.: 0.86 | J. Org. Chem. 2001, 66, 3196-3200 10.1021/jo0015927 | |
(bis(trimethylsiloxy)amino)styrene | dichloromethane | N Param.: 4.80 sN Param.: 0.86 | J. Org. Chem. 2001, 66, 3196-3200 10.1021/jo0015927 | |
2-(bis(tert-butyldimethylsiloxy)amino)propene | dichloromethane | N Param.: 4.23 sN Param.: 0.93 | J. Org. Chem. 2001, 66, 3196-3200 10.1021/jo0015927 | |
4-(bis(trimethylsiloxy)amino)pent-4-enoic acid methyl ester | dichloromethane | N Param.: 3.84 sN Param.: 0.87 | J. Org. Chem. 2001, 66, 3196-3200 10.1021/jo0015927 | |
anion of nitroethane (in DMSO) | DMSO | N Param.: 21.54 sN Param.: 0.62 | J. Org. Chem. 2003, 68, 6880-6886 10.1021/jo0344182 | |
anion of nitroethane (in water) | water | N Param.: 11.25 sN Param.: 0.52 | J. Org. Chem. 2004, 69, 7565-7576 10.1021/jo048773j | |
anion of nitromethane (in water) | water | N Param.: 12.06 sN Param.: 0.53 | J. Org. Chem. 2004, 69, 7565-7576 10.1021/jo048773j | |
anion of nitromethane (in DMSO) | DMSO | N Param.: 20.71 sN Param.: 0.60 | J. Org. Chem. 2004, 69, 7565-7576 10.1021/jo048773j | |
anion of 2-nitropropane (in DMSO) | DMSO | N Param.: 20.61 sN Param.: 0.69 | J. Org. Chem. 2004, 69, 7565-7576 10.1021/jo048773j | |
anion of 2-nitropropane (in water) | water | N Param.: 10.69 sN Param.: 0.56 | J. Org. Chem. 2004, 69, 7565-7576 10.1021/jo048773j | |
anion of phenylnitromethane (in H2O) | water | N Param.: 12.05 sN Param.: 0.53 | J. Org. Chem. 2004, 69, 7565-7576 10.1021/jo048773j | |
anion of phenylnitromethane (in DMSO) | DMSO | N Param.: 18.29 sN Param.: 0.71 | J. Org. Chem. 2004, 69, 7565-7576 10.1021/jo048773j | |
anion of p-tolylnitromethane (in water) | water | N Param.: 13.09 sN Param.: 0.50 | J. Org. Chem. 2004, 69, 7565-7576 10.1021/jo048773j | |
anion of p-tolylnitromethane (in DMSO) | DMSO | N Param.: 18.31 sN Param.: 0.76 | J. Org. Chem. 2004, 69, 7565-7576 10.1021/jo048773j | |
anion of (4-nitrophenyl)nitromethane (in water) | water | N Param.: 13.58 sN Param.: 0.52 | J. Org. Chem. 2004, 69, 7565-7576 10.1021/jo048773j | |
anion of (4-nitrophenyl)nitromethane (in DMSO) | DMSO | N Param.: 16.29 sN Param.: 0.75 | J. Org. Chem. 2004, 69, 7565-7576 10.1021/jo048773j | |
anion of (3-nitrophenyl)nitromethane (in water) | water | N Param.: 14.25 sN Param.: 0.46 | J. Org. Chem. 2004, 69, 7565-7576 10.1021/jo048773j | |
anion of (3-nitrophenyl)nitromethane (in DMSO) | DMSO | N Param.: 18.06 sN Param.: 0.71 | J. Org. Chem. 2004, 69, 7565-7576 10.1021/jo048773j | |
anion of (4-cyanophenyl)nitromethane (in water) | water | N Param.: 13.23 sN Param.: 0.52 | J. Org. Chem. 2004, 69, 7565-7576 10.1021/jo048773j | |
anion of (4-cyanophenyl)nitromethane (in DMSO) | DMSO | N Param.: 16.96 sN Param.: 0.73 | J. Org. Chem. 2004, 69, 7565-7576 10.1021/jo048773j | |
5-methoxy-indole | dichloromethane | N Param.: 6.22 sN Param.: 1.12 | J. Org. Chem. 2006, 71, 9088-9095 10.1021/jo0614339 | |
5-amino-indole | MeCN | N Param.: 7.22 sN Param.: 1.10 | J. Org. Chem. 2006, 71, 9088-9095 10.1021/jo0614339 | |
5-hydroxy-indole | MeCN | N Param.: 6.44 sN Param.: 1.10 | J. Org. Chem. 2006, 71, 9088-9095 10.1021/jo0614339 | |
5-methyl-indole | MeCN | N Param.: 6.00 sN Param.: 1.10 | J. Org. Chem. 2006, 71, 9088-9095 10.1021/jo0614339 | |
5-chloro-indole | MeCN | N Param.: 4.42 sN Param.: 1.10 | J. Org. Chem. 2006, 71, 9088-9095 10.1021/jo0614339 | |
5-bromo-indole | MeCN | N Param.: 4.38 sN Param.: 1.10 | J. Org. Chem. 2006, 71, 9088-9095 10.1021/jo0614339 | |
5-cyano-indole | MeCN | N Param.: 2.83 sN Param.: 1.10 | J. Org. Chem. 2006, 71, 9088-9095 10.1021/jo0614339 | |
1H-indole-5-carboxylic acid | MeCN | N Param.: 3.97 sN Param.: 1.10 | J. Org. Chem. 2006, 71, 9088-9095 10.1021/jo0614339 | |
5-methoxy-2-methylindole | MeCN | N Param.: 7.26 sN Param.: 1.10 | J. Org. Chem. 2006, 71, 9088-9095 10.1021/jo0614339 | |
2,5-dimethylindole | MeCN | N Param.: 7.22 sN Param.: 1.10 | J. Org. Chem. 2006, 71, 9088-9095 10.1021/jo0614339 | |
2-methylindole | MeCN | N Param.: 6.91 sN Param.: 1.10 | J. Org. Chem. 2006, 71, 9088-9095 10.1021/jo0614339 | |
5-chloro-2-methylindole | MeCN | N Param.: 6.08 sN Param.: 1.10 | J. Org. Chem. 2006, 71, 9088-9095 10.1021/jo0614339 | |
4-methoxy-indole | MeCN | N Param.: 5.41 sN Param.: 1.10 | J. Org. Chem. 2006, 71, 9088-9095 10.1021/jo0614339 | |
7-azaindole | MeCN | N Param.: 3.87 sN Param.: 1.10 | J. Org. Chem. 2006, 71, 9088-9095 10.1021/jo0614339 | |
anion of 4-(trifluoromethyl)benzyl-CN (in DMSO) | DMSO | N Param.: 27.28 sN Param.: 0.50 | J. Org. Chem. 2009, 74, 75-81 10.1021/jo802241x | |
anion of 4-cyanobenzyl-CN (in DMSO) | DMSO | N Param.: 25.11 sN Param.: 0.54 | J. Org. Chem. 2009, 74, 75-81 10.1021/jo802241x | |
anion of 4-nitrobenzyl-CN (in DMSO) | DMSO | N Param.: 19.67 sN Param.: 0.68 | J. Org. Chem. 2009, 74, 75-81 10.1021/jo802241x | |
anion of 2-phenyl-propionitrile (in DMSO) | DMSO | N Param.: 28.95 sN Param.: 0.58 | J. Org. Chem. 2009, 74, 75-81 10.1021/jo802241x | |
anion of 2-(4-CN-C6H4)propionitrile (in DMSO) | DMSO | N Param.: 25.35 sN Param.: 0.56 | J. Org. Chem. 2009, 74, 75-81 10.1021/jo802241x | |
anion of 2-(4-NO2-C6H4)propionitrile (in DMSO) | DMSO | N Param.: 19.61 sN Param.: 0.60 | J. Org. Chem. 2009, 74, 75-81 10.1021/jo802241x | |
chloro(phenylsulfonyl)methanide (in DMSO) | DMSO | N Param.: 28.27 sN Param.: 0.42 | J. Org. Chem. 2017, 82, 2011-2017 10.1021/acs.joc.6b02844 | |
bromo(phenylsulfonyl)methanide (in DMSO) | DMSO | N Param.: 23.90 sN Param.: 0.62 | J. Org. Chem. 2017, 82, 2011-2017 10.1021/acs.joc.6b02844 | |
chloro((4-cyanophenyl)sulfonyl)methanide (in DMSO) | DMSO | N Param.: 25.59 sN Param.: 0.51 | J. Org. Chem. 2017, 82, 2011-2017 10.1021/acs.joc.6b02844 | |
chloro((4-nitrophenyl)sulfonyl)methanide (in DMSO) | DMSO | N Param.: 24.88 sN Param.: 0.49 | J. Org. Chem. 2017, 82, 2011-2017 10.1021/acs.joc.6b02844 | |
chloro((4-chlorophenyl)sulfonyl)methanide (in DMSO) | DMSO | N Param.: 26.90 sN Param.: 0.45 | J. Org. Chem. 2017, 82, 2011-2017 10.1021/acs.joc.6b02844 | |
barbiturate anion (in DMSO) | DMSO | N Param.: 15.59 sN Param.: 0.80 | J. Org. Chem. 2017, 82, 8476-8488 10.1021/acs.joc.7b01223 | |
1,3-dimethylbarbiturate anion (in DMSO) | DMSO | N Param.: 17.46 sN Param.: 0.72 | J. Org. Chem. 2017, 82, 8476-8488 10.1021/acs.joc.7b01223 | |
2-thiobarbiturate anion (in DMSO) | DMSO | N Param.: 14.24 sN Param.: 0.82 | J. Org. Chem. 2017, 82, 8476-8488 10.1021/acs.joc.7b01223 | |
1,3-diethyl-thiobarbiturate anion (in DMSO) | DMSO | N Param.: 14.90 sN Param.: 0.80 | J. Org. Chem. 2017, 82, 8476-8488 10.1021/acs.joc.7b01223 | |
1,3-dimethyl-2-methyleneimidazolidine (in THF) | THF | N Param.: 18.11 sN Param.: 0.68 | J. Org. Chem. 2021, 86, 2974-2985 10.1021/acs.joc.0c02838 | |
1,3-dimethyl-2-methylenehexahydropyrimidine (in THF) | THF | N Param.: 18.68 sN Param.: 0.63 | J. Org. Chem. 2021, 86, 2974-2985 10.1021/acs.joc.0c02838 | |
1,3-dimesityl-2-methylene-2,3-dihydro-1H-imidazole (in THF) | THF | N Param.: 17.80 sN Param.: 0.79 | J. Org. Chem. 2021, 86, 2974-2985 10.1021/acs.joc.0c02838 | |
1,3-dimethyl-2-methylene-2,3-dihydro-1H-benzo[d]imidazole | THF | N Param.: 19.84 sN Param.: 0.58 | J. Org. Chem. 2021, 86, 2974-2985 10.1021/acs.joc.0c02838 | |
toluene | dichloromethane | N Param.: -4.36 sN Param.: 1.77 | J. Am. Chem. Soc. 2012, 134, 13902-13911 10.1021/ja306522b | |
m-xylene | dichloromethane | N Param.: -3.57 sN Param.: 2.08 | J. Am. Chem. Soc. 2001, 123, 9500-9512 10.1021/ja010890y | |
(E)-propenylbenzene | dichloromethane | N Param.: -0.49 sN Param.: 1.18 | J. Am. Chem. Soc. 2012, 134, 13902-13911 10.1021/ja306522b | |
2-methylthiophene | dichloromethane | N Param.: 1.35 sN Param.: 0.99 | J. Am. Chem. Soc. 2012, 134, 13902-13911 10.1021/ja306522b |